Sodium Methoxide → methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 269487ノート

反応式

HRID 269487 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11](S(C3C=CC(C)=CC=3)(=O)=O)[C:8]2=[N:9][CH:10]=1)=[O:4].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 497589101H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, methyl ester

生成物 1

HCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
65 °C

実験手順

A suspension of 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (5.4 g, 16 mmol) in MeOH (100 mL) with NaOMe in MeOH (20 mL, 25% wt., excess) was heated at 65° C. for 1 hour. The resulting material was concentrated from MeOH, diluted with H2O (100 mL), and pH adjusted to 6 with 1N HCl. The aqueous solution was partitioned with EtOAc (100 mL) and the organic extraction was dried over Na2SO4 and dried in vacuo. The residue was purified with flash chromatography over silica gel in an elution from 99:1 CH2Cl2:MeOH to 92:8 CH2Cl2:MeOH. Yield 1.8 g, beige powder.

後処理

  1. concentrationThe resulting material was concentrated from MeOH
  2. additiondiluted with H2O (100 mL)
  3. customThe aqueous solution was partitioned with EtOAc (100 mL)
  4. extractionthe organic extraction
  5. dry with materialwas dried over Na2SO4
  6. customdried in vacuo
  7. customThe residue was purified with flash chromatography over silica gel in an elution from 99:1 CH2Cl2

出典と根拠

ORDレコード
ord-59a2f3afe7ea4e7fbe027a78e15530c6
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

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